YYZ - SXM

$126 Find Cheap Flights from Toronto to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto to Simpson Bay departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Simpson Bay, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Toronto to Simpson Bay (YYZ-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto to Simpson Bay

Sat, Jan 3 - Fri, Jan 16
American Airlines Logo
5:19 pm - 1:59 pmYYZ-SXM
19h 40m2 stops
American Airlines Logo
5:20 pm - 11:05 amSXM-YYZ
18h 45m2 stops
$368American Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 18
United Airlines Logo
7:40 pm - 1:50 pmYYZ-SXM
17h 10m2 stops
United Airlines Logo
4:55 pm - 11:46 pmSXM-YYZ
7h 51m1 stop
$370United Airlines
Find Deal
Sun, Nov 30 - Thu, Dec 4
WestJet Logo
9:30 am - 3:21 pmYYZ-SXM
4h 51mnonstop
WestJet Logo
4:20 pm - 8:43 pmSXM-YYZ
5h 23mnonstop
$371WestJet
Find Deal
Sat, Oct 25 - Thu, Oct 30
United Airlines Logo
2:45 pm - 2:57 pmYYZ-SXM
24h 12m1 stop
United Airlines Logo
1:52 pm - 11:20 pmSXM-YYZ
9h 28m1 stop
$377United Airlines
Find Deal
Sat, Dec 6 - Thu, Dec 11
Air Transat Logo
6:30 am - 12:15 pmYYZ-SXM
4h 45mnonstop
Air Transat Logo
1:05 pm - 8:52 pmSXM-YYZ
8h 47m1 stop
$383Air Transat
Find Deal
Sun, Nov 30 - Sun, Dec 7
WestJet Logo
9:30 am - 3:21 pmYYZ-SXM
4h 51mnonstop
WestJet Logo
4:20 pm - 8:43 pmSXM-YYZ
5h 23mnonstop
$387WestJet
Find Deal
Sat, Nov 1 - Sat, Nov 8
Air Transat Logo
6:30 am - 11:15 amYYZ-SXM
4h 45mnonstop
Air Transat Logo
1:25 pm - 5:50 pmSXM-YYZ
5h 25mnonstop
$390Air Transat
Find Deal
Tue, Jan 20 - Tue, Feb 17
 Logo
9:30 am - 3:21 pmYYZ-SXM
4h 51mnonstop
 Logo
1:25 pm - 5:50 pmSXM-YYZ
5h 25mnonstop
Tue, Jan 20 - Tue, Feb 17
Air Canada Logo
4:00 pm - 1:50 pmYYZ-SXM
20h 50m2 stops
Air Canada Logo
5:00 pm - 9:15 pmSXM-YYZ
5h 15mnonstop
$455Air Canada
Find Deal
Sat, Jan 3 - Fri, Jan 16
 Logo
6:30 am - 12:15 pmYYZ-SXM
4h 45mnonstop
 Logo
4:20 pm - 8:43 pmSXM-YYZ
5h 23mnonstop

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Air Canada offers Wi-Fi on select flights to Simpson Bay.
WestJet allows bidding on upgrades for Premium seats.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
American Airlines
Cheapest • from $368 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 22% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 20% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
6 days a week
There are direct flights from Toronto to Simpson Bay 6 days a week: Mon, Tue, Thu, Fri, Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
Cheapest round-trip
$368
Typical prices: $392-551
American Airlines
Sat 1/3Fri 1/16
YYZ - SXM • 2 stops
Cheapest non-stop
$371
Typical prices: $394-699
WestJet
Sun 11/30Thu 12/4
YYZ - SXM • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Expert advice

Expert advice for your flight from Toronto to Simpson Bay

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
WestJet

WestJet's Premium cabin offers extra legroom and priority boarding on narrowbody aircraft.


WestJet allows bidding on upgrades for Business or Premium seats before your flight.

Read more about WestJetby Stefanie Waldek
Air Transat

Air Transat's Club Class offers wider seats and more legroom than economy.


Air Transat provides in-flight entertainment on most flights, bring headphones with a 3.5mm plug.

Air Canada

Air Canada offers priority boarding for Premium Economy and elite status passengers.


Air Canada provides Wi-Fi on select flights, check availability five days before departure.

Read more about Air Canadaby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet and Air Canada

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
John Walton

John Walton

Expert on Air Transat

John Walton

John Walton

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more
Booking Insights

KAYAK's insights & trends for Toronto to Simpson Bay flights

Get data-powered insights and trends into flights from Toronto to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Toronto Pearson Intl Airport to Simpson Bay?

What’s the cheapest day of the week to fly from Toronto to Simpson Bay?

The average price of all round-trip flights from Toronto Pearson Intl Airport to Simpson Bay clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Simpson Bay on a Tuesday and more expensive on a Wednesday. On your return trip to Toronto, you should consider flying back on a Saturday, and avoid Mondays for better deals.

What is the cheapest month to fly from Toronto Pearson Intl Airport to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Pearson Intl Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Toronto Pearson Intl Airport to Simpson Bay is September, where tickets cost $396 (return) on average. On the other hand, the most expensive months are August and December, where the average cost of round-trip tickets is $579 and $577 respectively.

Can I save money by flying with a layover from Toronto Pearson Intl Airport to Simpson Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $523 on average.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Simpson Bay?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Toronto Pearson Intl Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Toronto Pearson Intl Airport to Simpson Bay, you should book around 3 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$126
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Toronto to Simpson Bay

When to book flights from Toronto to Simpson Bay

Are your dates flexible? Find out the best times to travel from Toronto to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Toronto to Simpson Bay flights

  • What is the cheapest flight from Toronto Pearson Intl Airport to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Simpson Bay was $126 for a one-way ticket and $368 for a round-trip.

  • Do I need a passport to fly between Toronto and Simpson Bay?

    A passport is required to fly from Toronto to Simpson Bay.

  • Which airlines offer Wi-Fi service onboard planes from Toronto to Simpson Bay?

    Air Canada, and WestJet offer inflight Wi-Fi service on the Toronto to Simpson Bay flight route.

  • Which aircraft models fly most regularly from Toronto to Simpson Bay?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Toronto to Simpson Bay flight route.

  • On which days can I fly direct from Toronto to Simpson Bay?

    You can catch a nonstop flight from Toronto to Simpson Bay on Sunday.

  • Which is the best airline for flights from Toronto to Simpson Bay, Delta or Air Transat?

    The two airlines most popular with KAYAK users for flights from Toronto to Simpson Bay are Delta and Air Transat. With an average price for the route of $609 and an overall rating of 7.9, Delta is the most popular choice. Air Transat is also a great choice for the route, with an average price of $555 and an overall rating of 7.7.

  • How does KAYAK find such low prices on flights from Toronto to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Toronto is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Toronto with another airline. Booking your flights between Toronto and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Toronto up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Toronto Pearson Intl Airport to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $144 or less one-way and $491 or less round-trip.

Prefer to fly direct from Toronto to Simpson Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto Pearson Intl to Simpson Bay Princess Juliana.
Find which airlines fly direct from Toronto Pearson Intl Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Toronto Pearson Intl to Simpson Bay Princess Juliana

Monday

WestJet

WestJet

Tuesday

WestJet

WestJet

Thursday

WestJet

WestJet

Friday

Air Canada, WestJet

Air Canada, WestJet

Saturday

Air Canada, Air Transat

Air Canada, Air Transat

Sunday

WestJet

WestJet

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Toronto Pearson Intl

Monday

WestJet

WestJet

Tuesday

WestJet

WestJet

Thursday

WestJet

WestJet

Friday

Air Canada, WestJet

Air Canada, WestJet

Saturday

Air Canada, Air Transat

Air Canada, Air Transat

Sunday

WestJet

WestJet

See more direct flights

Reviews of the top 5 airlines serving from Toronto to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Toronto to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 7956 reviews
7.3Food
7.9Entertainment
7.9Comfort
8.5Crew
8.2Boarding
Airline reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

4.0 Okaypuravi, Aug 2025LGA - STL
Read more Delta reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

It was beautiful easy and smooth experience. Thank you. Will definitely get Delta for my next travel.

The way BCN airport handled boarding was a huge improvement over our trip to Spain from JFK. Instead of gate-mosquitos edging in before their zone was called, in BCN they had clearly marked lines for Zones 1-8 and people just lined up correctly. The flight itself was uneventful. The meal (curried chicken and rice) was one of the better meals we've had on Delta. Entertainment options were plentiful, power chargers were available in Main Cabin, and seats were decent. Flight staff were very friendly and positive throughout the 8 hour flight.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

After I checked in, I realized we had no seat assignment. It said they would be assigned at the gate. This was really frustrating because I usually use a lounge before flights, but I couldn't because I had to be at the gate to ensure we got our seat assignments. The gate agent arrived an hour before the flight left. I was the first one up to ask about seat assignments. She told us to wait for names to be called. Dozens of other passengers were paged, but we were not. Finally, I asked my husband to ask. He went up and was also told to wait. About 10 minutes later, they called for boarding. We still had not been told our seats. We went back to the desk and they were in a panic, saying we actually weren't on that flight. Then they made an announcement telling the stand by passengers to not board (in case we needed their seats). It was so stressful and unprofessional. Finally they gave us our seats. I have no idea what happened and why the two desk agents seemed to have conflicting ideas about our seats, whether we were on that flight etc.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Friendly crew, quick boarding. We even arrived a few minutes earlier than our original flight plan. No onboard screens, but it’s a relatively short flight so it’s not really an issue.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Very dissatisfied with the fact that I had upgraded to first class for the second part of my trip only to find out that the lounge was still not available to me, as well as not having any food or drink service on the flight due to weather, so I lost out more than what I paid for.

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

The crew were polite and courteous. The Pilot did an excellent landing. It was very smooth and gentle. My only regret is that I was charged twice for my luggage . The attendant gave me no receipt . I didn't realize until I was about to board. How can this be resolved? Thank you.

Very smooth flights Toronto to Rome and return. Crews were great, food was fine but very narrow seats and limited leg room. Aisle seats on our return helped with a bit more space.

YUL AIRPORT is the worst. 1 Hr to Get out of the plane, 1 Hr To Cross the Border. 1Hr waiting to be pick up curbside. Trafic is ubeliveble.

It’s ok just the boarding point is far too far

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Good service, friendly staff. Food was average for airlines and the seats were small.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm

Mechanical delay and no compensation. Missed connection as a result of their delay. Mediocre performance and service. Horrible airline currently with horrible culture.

They cancelled my flight and downgraded me to economy and only gave me $250 for the downgrade

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

Not very good , the stewardess were unfriendly and they don't like to be bothered. Cos was a night flight and they need to sleep.

I like how spacious the plane was but I did not like the fact that there was no entertainment

No dogs! Can we have no dogs in the cabin? Why was there a yappy little dog behind me? Lucky I had ear plugs. Sorry for others without

In spite of purchasing premium, I felt it was perhaps the most uncomfortable seat I have flown in. The base was either broken or poorly made and had no support. Even placing pillows and blankets on the seat (1D aisle) didn’t help. It made for a long and mostly sleepless six hour flight. Crew also were very loudly talking to each other through the night making it very hard to sleep. It was purchased for the price, so I get the risk, but was not impressed.

Good value, minor delay due to waiting for inbound plane but they gave accurate information about wait time. Able to switch to a seat by my husband thanks to a kind flight attendant

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

Arrival at Comox from, London,ON 6 hours later... No bueano

Generally good. However. The flight left 30 mins behind schedule with no reason given.

Flight delayed, missed my pick-up had to Uber, plus missed dinner and medication, so sad!

Nothing to like because my inbound flight was cancelled without notification by West Jet or third party, JustFly. I couldn’t take the inbound flight due to cancellation; therefore could not take the outbound flight back.

Not the greatest experience everything was pretty mediocre. My seat was by the washroom in the aisle and was not located well as everyone past each other people were right in my seat and space.

The crew were fabulous. The flight was bumpy and I always like the captain to tell me what that is about or my imagination gets carries away.

I liked the behaviour of the crew members.The flight was good.

Food can be better. Taste and option, the pasta wasn't the greatest.

The internet connection was perfect, and the updated entertainment systems that allow me to connect my Bluetooth earbuds was excellent

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

It was good to receive a card for my birthday

Horrible flight cancelled had to buy another very expensive ticket

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Everything you need to know for your flight from Toronto to Simpson Bay

Information on your arrival and departure airports

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